Jack is Charlie's penis and he is the brains of the operation. He and Charlie have been friends from birth. When Charlie meets Barbie Le Fleur, a Canadian transfer student, Jack will do everything in his power to guide his friend in his quest to enchant his dream girl. With the help of an odd group of characters; from an incredibly handsome school therapist to a sex advisor prostitute and a group of hormonal friends, Charlie will use his "brain" to get the girl of his dreams.